Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of organic small molecule fluorescent probe

A technology for fluorescent probes and small molecules, which is applied in the field of preparation of novel near-infrared second-region fluorescent small molecules, can solve the problems of high requirements for testing instruments, complicated probe synthesis steps, low fluorescence quantum yield, etc. The effect of steric hindrance, shortened product preparation time, and high fluorescence quantum yield

Active Publication Date: 2022-03-11
NANJING NUOYUAN MEDICAL DEVICES CO LTD
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Generally, organic near-infrared second-region fluorescent small molecules are mainly divided into three categories. The first type is a near-infrared second-region fluorescent small molecule with a benzobisthiadiazole structure as the main body. This probe has a high fluorescence quantum yield, but the probe The synthesis steps are cumbersome, and the synthesis requires the use of highly toxic tin reagents
The second type is a near-infrared second-region fluorescent small molecule with polymethyl as the main body. It is mainly an extension of the near-infrared first-region cyanine dye probe and replaces the electron-donating group. lower decomposition, and the quantum yield is lower
The third category is to study cyanine dyes, which have fluorescence tailing at 1000-1200nm, and the fluorescence quantum yield is extremely low, which requires high requirements for testing instruments

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of organic small molecule fluorescent probe
  • A kind of preparation method of organic small molecule fluorescent probe
  • A kind of preparation method of organic small molecule fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A method for preparing an organic small molecule fluorescent probe, comprising the following steps:

[0043] A, the synthesis of intermediate-1

[0044] Add N,N-dimethylformamide, 1,8-naphtholactam (100.0g, 0.59mol) and potassium carbonate (10g) into the stirred reactor, heat up to 115°C under stirring, nitrogen Under the protection, weighed 1,3-dibromopropane (240g, 1.18mol) was added dropwise, and the reaction was incubated for 3.5 hours. Subsequently, it was extracted twice with ethyl acetate (1000ml), and the extract was washed with saturated brine and added Na 2 SO 4 Dry the water, distill off the solvent and other low-boiling organic components under reduced pressure to obtain the crude product 1, and separate the crude product 1 on a silica gel column, and the eluent is a mixture of petroleum ether: ethyl acetate (1:10) to obtain the intermediate A M1 product 157.0g (98.4%), yield 90.1%.

[0045]

[0046] B, the synthesis of intermediate two M2

[0047] Diss...

Embodiment 2

[0060] Based on Example 1, a method for preparing an organic small molecule fluorescent probe, wherein the steps:

[0061] A, the synthesis of intermediate-M1

[0062] Add N,N-dimethylformamide, 1,8-naphtholactam (100.0g, 0.59mol) and potassium carbonate (10g) into a stirred reaction kettle, heat up to 118°C under stirring, nitrogen Under the protection, weighed 1,3-dibromopropane (240g, 1.18mol) was added dropwise, and the reaction was incubated for 3.5 hours. Subsequently, it was extracted twice with ethyl acetate (1000ml), and the extract was washed with saturated brine and added Na 2 SO 4 The moisture was dried, the solvent and other low-boiling organic components were distilled off under reduced pressure, and the crude product was separated on a silica gel column. The eluent was a mixture of petroleum ether: ethyl acetate (1:10) to obtain 158.5 g of an intermediate-M1 product ( 98.2%), yield 90.9%.

Embodiment 3

[0064] Based on Example 1, a method for preparing an organic small molecule fluorescent probe, wherein the steps:

[0065] A, the synthesis of intermediate-M1

[0066] Add N,N-dimethylformamide, 1,8-naphtholactam (100.0g, 0.59mol) and potassium carbonate (10g) into the stirred reactor, heat up to 120°C under stirring, nitrogen Under the protection, weighed 1,3-dibromopropane (240g, 1.18mol) was added dropwise, and the reaction was incubated for 3.5 hours. Subsequently, it was extracted twice with ethyl acetate (1000ml), and the extract was washed with saturated brine and added Na 2 SO 4 Dry the water, distill off the solvent and other low-boiling point organic components under reduced pressure. The crude product is separated on a silica gel column. The eluent is a mixture of petroleum ether: ethyl acetate (1:10) to obtain 157.2 g of an intermediate-M1 product ( 98.7%), yield 90.6%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing an organic small molecule fluorescent probe. A novel structural fluorescent probe small molecule is constructed and prepared by an organic total synthesis method, which belongs to the field of chemical sensing technology and fluorescence imaging. Compared with the fluorescent probe of benzobisthiadiazole structure, which has been studied more at present, this organic small molecule fluorescent probe has the advantages of simple synthesis method, easy modification, stable structure and high fluorescence quantum yield.

Description

technical field [0001] The invention provides a method for preparing a novel fluorescent small molecule in the second near-infrared region, and relates to the fields of fluorescent probe detection technology, fluorescent imaging technology and the like. Background technique [0002] Fluorescence microscopy imaging technology is one of the most widely used technologies in current optical imaging technology, and near-infrared fluorescence in vivo imaging technology, which is also fluorescence imaging, is also attracting more and more attention in the field of biomedicine. Traditional fluorescence imaging is mainly concentrated in the near-infrared region (NIR-I), the fluorescence emission wavelength range is 650-950nm, the wavelength is relatively short (<1000nm), and the photon penetration depth is poor, which has become the main obstacle for the application of in vivo biomedical fluorescence imaging . Compared with visible light and NIR-I light, the wavelength is in the ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C09K11/06G01N21/64
CPCC07D495/04C09K11/06G01N21/6456G01N21/6428C09K2211/1029C09K2211/1096
Inventor 蔡惠明王毅庆
Owner NANJING NUOYUAN MEDICAL DEVICES CO LTD